PtCl(2)-catalyzed cycloisomerization of 1,6-enynes for the synthesis of substituted bicyclo[3.1.0]hexanes

The Journal of Organic Chemistry
Liu YeVéronique Michelet

Abstract

The mild and efficient PtCl(2)-catalyzed cycloisomerization of 1,6-enynes containing a heteroatom substituent at the propargylic position is described. The reactions led to the formation of 1-alkenylbicyclo[3.1.0]hexanes in good to excellent yields or 2-(bicyclo[3.1.0]hex-1-yl)acetaldehydes in moderate yields.

References

Oct 25, 2001·Journal of the American Chemical Society·M MéndezA M Echavarren
Nov 29, 2001·Journal of the American Chemical Society·A FürstnerH Szillat
Sep 18, 2002·Accounts of Chemical Research·Barry M Trost
Mar 11, 2004·Chemical Reviews·Steven T Diver, Anthony J Giessert
Apr 29, 2004·Angewandte Chemie·Cristina Nieto-OberhuberAntonio M Echavarren
Jul 15, 2004·Journal of the American Chemical Society·Victor MamaneAlois Fürstner
Jul 15, 2004·Journal of the American Chemical Society·Youssef HarrakMax Malacria
Aug 28, 2004·Organic Letters·Cristina NevadoAntonio M Echavarren
Sep 2, 2004·Journal of the American Chemical Society·Michael R LuzungF Dean Toste
Sep 9, 2004·Chemical Society Reviews·Antonio M Echavarren, Cristina Nevado
Nov 6, 2004·The Journal of Organic Chemistry·Elena SorianoJosé Marco-Contelles
Sep 8, 2005·Angewandte Chemie·Cristina Nieto-OberhuberAntonio M Echavarren
Nov 5, 2005·The Journal of Organic Chemistry·Elena Soriano, José Marco-Contelles
Dec 13, 2005·Angewandte Chemie·Shengming MaZhenhua Gu
Dec 17, 2005·Chemistry : a European Journal·Cristina Nieto-OberhuberAntonio M Echavarren
Jun 7, 2006·Chemistry : a European Journal·Cristina Nieto-OberhuberAntonio M Echavarren
Jul 27, 2006·Journal of the American Chemical Society·Jianwei SunSergey A Kozmin
Nov 30, 2006·Angewandte Chemie·A Stephen K Hashmi, Graham J Hutchings
Apr 13, 2007·Angewandte Chemie·Alois Fürstner, Paul W Davies
Jun 22, 2007·Chemical Reviews·A Stephen K Hashmi
Dec 14, 2007·Journal of the American Chemical Society·Cristina Nieto-OberhuberAntonio M Echavarren
Apr 3, 2008·Angewandte Chemie·Véronique MicheletJean-Pierre Genêt
Jul 11, 2008·Chemical Reviews·Zigang LiChuan He
Jul 18, 2008·Journal of the American Chemical Society·Masashi ToyofukuNobuaki Kambe
Jul 19, 2008·Chemical Reviews·Eloísa Jiménez-Núñez, Antonio M Echavarren
Jan 6, 2009·Chemistry : a European Journal·Chung-Meng ChaoVéronique Michelet
Feb 12, 2009·Journal of the American Chemical Society·Yoshikazu HorinoF Dean Toste
Nov 12, 2009·Chemical Communications : Chem Comm·Chung-Meng ChaoVéronique Michelet

❮ Previous
Next ❯

Citations

Sep 15, 2011·Beilstein Journal of Organic Chemistry·Alexandre PradalVéronique Michelet
May 21, 2016·Natural Product Reports·Christos I StathakisAlexandros L Zografos
Jun 27, 2014·Chemistry : a European Journal·Hye Mi OhYoung Keun Chung
Mar 8, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Hsuan YangYi-Hong Liu
May 17, 2012·Chemistry : a European Journal·Frédéric MiegeJanine Cossy
Jun 20, 2012·Angewandte Chemie·Theo D MichelsChristopher D Vanderwal
May 16, 2014·Journal of the American Chemical Society·Koji MasutomiKen Tanaka

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.